Synthesis of linezolid metabolites PNU-142300 and PNU-142586 toward the exploration of metabolite-related events

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Linezolid (1) is an oxazolidinone antibiotic that is partially metabolized in vivo via ring cleavage of its morpholine moiety to mainly form two metabolites, PNU-142300 (2) and PNU-142586 (3). It is supposed that accumulation of 2 and 3 in patients with renal insufficiency may cause thrombocytopenia, one of the adverse effects of linezolid. However, the poor availability of 2 and 3 has hindered further investigation of the clinical significance of the accumulation of these metabolites. In this paper, we synthesized metabolites 2 and 3 via a common synthetic intermediate, 4; this will encourage further exploration of events related to these metabolites and lead to improved clinical use of linezolid.

Original languageEnglish
Pages (from-to)194-199
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Issue number2
Publication statusPublished - 2017



  • Linezolid
  • Metabolite
  • Oxazolidinone
  • Tetrabutylammonium salt
  • Thrombocytopenia

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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